(S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-pyridinyl)ethanol → (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-piperidinyl)ethanol

HRID 2074415Notes

Reaction equation

HRID 2074415 reaction equation
[CH:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[OH:14])([CH3:3])[CH3:2]>O=[Pt]=O.CC(O)=O>[CH:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][C@@H:13]([CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1)[OH:14])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58870080(S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-pyridinyl)ethanol

Product 1

HCID 58870110(S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-piperidinyl)ethanol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Shake a mixture of (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-pyridinyl)ethanol (21.1 g, 78 mmol), HOAc (400 mL) and PtO2 (370 mg) with H2 (50 psi) for 15 hr. Filter the mixture through celite and evaporate the solvent to give (S)-2-(2-isopropoxy-3-methylphenyl)-1-(4-piperidinyl)ethanol as the acetate salt; 1H-NMR (CDCl3) δ 7.1-6.9 (m, 2H), 4.2 (m, 1H), 3.6 (m, 1H), 3.4 (m, 2H), 2.9-2.7 (m, 4H), 2.3 (s, 3H), 2.0 (s, 3H), 2.1-1.5 (m, 5H), 1.3 (d, 6H).

Workup

  1. filtrationFilter the mixture through celite
  2. customevaporate the solvent

Sources & evidence

ORD record
ord-3131b9ce416f45ffab58679eb0ab5474
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

Loading…